Gracious Prestige Landmark ~ 2 Private Beaches ~ Fabulous View

Photo gallery for Gracious Prestige Landmark ~ 2 Private Beaches ~ Fabulous View

A covered deck with a wooden table and chairs, overlooking a scenic landscape.
A large, two-story house with a red roof, surrounded by a well-maintained lawn and a view of a lake.
A spacious living room with a large window, a bookshelf, and a sailboat model.
A traditional living room with a fireplace, two armchairs, a coffee table, and a staircase leading to another room.
A kitchen with a dining area, wooden cabinets, a microwave, and a view through large windows.

Reviews

10 out of 10
Exceptional

Highlights

  • Scenic water view
    Relax and unwind with top-rated water views, offering a scenic experience.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Patio
  • Barbecue
  • Air-conditioning
  • Pet-friendly
  • Refrigerator
  • Washing machine

Explore the area

View map
Chilmark, MA
  • Place, Squibnocket Pond
    ‪13 min walk‬
  • Place, Menemsha Beach
    ‪12 min drive‬
  • Place, Inkwell Beach
    ‪41 min drive‬
  • Airport, Vineyard Haven, MA (MVY-Martha's Vineyard)
    ‪27 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Double Bed

Bedroom 5

2 Single Beds

3 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Garden

Add dates for prices

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  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
10.0 out of 10, Exceptional, (36 reviews)
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About the area

Chilmark

Located in Chilmark, this holiday home is in a rural area and near the beach. Island Cove Miniature Golf and Island Cove Adventures are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chilmark Chocolates and Fulling Mill Brook Preserve. The Grey Barn and Farm and Polly Hill Arboretum are also worth visiting. Waterskiing and windsurfing offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and cycling nearby.
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Map
Chilmark, MA

What's nearby

  • Squibnocket Pond - 13 min walk - 1.1 km
  • Menemsha Beach - 12 min drive - 8.8 km
  • Oak Bluffs Harbor - 39 min drive - 34.5 km
  • Oak Bluffs Town Beach - 40 min drive - 35.2 km
  • Inkwell Beach - 41 min drive - 35.2 km

Getting around

  • Vineyard Haven, MA (MVY-Martha's Vineyard) - 19 min drive

Restaurants

  • ‪Chilmark Tavern - ‬4 min drive
  • ‪Menemsha Galley - ‬8 min drive
  • ‪Home Port Restaurant - ‬7 min drive
  • ‪Aquinnah Shop - ‬6 min drive
  • ‪The Homeport - ‬7 min drive

Frequently asked questions

Is Gracious Prestige Landmark ~ 2 Private Beaches ~ Fabulous View pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Gracious Prestige Landmark ~ 2 Private Beaches ~ Fabulous View?

On-site parking is available at the property.

What time is check-in at Gracious Prestige Landmark ~ 2 Private Beaches ~ Fabulous View?

Check-in begins at 4:00 PM.

What time is check-out at Gracious Prestige Landmark ~ 2 Private Beaches ~ Fabulous View?

Checkout is at 10:00 AM.

Where is Gracious Prestige Landmark ~ 2 Private Beaches ~ Fabulous View located?

Situated by the sea, this holiday home is 0.5 mi (0.9 km) from Squibnocket Pond and within 3 miles (5 km) of Stonewall Beach and Chilmark Chocolates. Chilmark Town Hall and Chilmark Public Library are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 23 out of 25 reviews
Rating 8 - Good. 2 out of 25 reviews
Rating 6 - Okay. 0 out of 25 reviews
Rating 4 - Poor. 0 out of 25 reviews
Rating 2 - Terrible. 0 out of 25 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

We had a wonderful visit! Such a great family house that wonderful memories were made at. We will definitely return!
Stayed 7 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

What a view!

Our extended family had a great time, thank you
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A magical week with three generations, the whole family, ages 1 - 70. The house wraps its arms around you, and there is room in the big kitchen for all the cooks and all the eaters. Fabulous yard for playing games, flying kites, the kiddie pool we brought and a perfect hammock. We hope to go back in a few years when the grandchildren are bigger, it will still be a perfect spot!
Stayed 9 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Old Vineyard at its best

This charming Vineyard icon was perfect for a large family gathering. Plenty of room to spread out, sweeping lawns for children to play, and lots of nooks and crannies for a rainy day.
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Airy Victorian with idyllic views

Stayed for a week with my wife, children, cousin and his family. Lovely experience in charming location. Spacious, airy, commanding property with romantic sea views. I highly recommend for large family groups. Like having a B&B to yourselves. Host was highly communicative. Access to private Beach.
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful, spacious home

The house was fabulous for us, plenty of room, beautiful views, well equipped, comfortable spacious bedrooms, great big lawn, lovely porch and deck and perfect location.
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Unbelievable 270 degree view on the back patio was shocking beautiful every morning and evening. With teenagers who can drive at home but not rentals I think being in Edgartown or Oak Bluffs would have been better but for adults and kids chilmark is laid back and gorgeous. Private beach was beautiful, large, and largely empty. House was beautiful in that old vineyard way. Special.
Stayed 4 nights in Aug 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chilmark Tower House Family Vacation

We enjoyed our stay at Tower House, certainly enough room for our family, ages ranging from 10 months to 94. The views from the back patio out to Menemsha Pond and Vineyard Sound beyond were spectacular, just a wonderful spot for a morning coffee or evening cocktail when the weather is right. The house was well stocked with towels, dishes, cookware and glassware and we even made use of the lobster pot. Access to the private ocean beach was great.
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

great house

Beautiful house with the BEST view and amazing yard! We had an excellent stay. Absolutely incredible- loved it so much!! One thing to note for others inquiring is that the guest house is very close to main house and was rented by a different group while we were there. If this is a consideration for you, then likely would check in with owners as to whether it will be occupied.
Stayed 7 nights in Aug 2024
Archival

10/10 Excellent

It was wonderful as always

The house has great views and delightful sea breezes. It is always relaxing to enjoy the slower pace of life, the farmers market twice a week in West Tisbury, the wonderful fresh fish from the fish market in Menemsha, a trip into Vineyard Haven or Edgartown to walk along the main street and enjoy the shops, and to wander down along the harbor and watch the boats. There is always something going on around the Island, or you can just sit on the back porch and enjoy the view of Menemsha Pond and Vineyard Sound. There are good restaurants in all the towns to discover, sample, and enjoy. We always look forward to our time every summer at the house!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Once again, a great stay!

This is our second summer stay at this house, and it was as perfect as it was the last time. The water views from the back of the house, particularly from the fabulous deck, are unmatched on the rest of the island. The house is perched high on land that connects Chilmark to Aquinnah so offers an amazing bucolic vista of pastures and meadows ringed by stone walls, down to Menemsha Pond and Vineyard Sound in the distance. The feeling is very rural and relaxing. There are lots of beaches to explore, many of them noticeably less populated than those on the rest of the island. There is no air conditioning, but you don’t need it because, being at a high point geographically, it has nice breezes all the time.
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends and Family

We had an awesome week at the Tower House in Chilmark. The house itself housed our two families (4 adults and 6 2nd grade to baby boys) with ease. Everyone had space both inside and out. The kids ran through the grass, played in the hammock and ate dinner watching deer and boats in the distance. We enjoyed the porch, kitchen and back deck. Bob was in close contact and Charlie the caretaker was a fast and lovely resource. The gem of this property is the key to Hancock Beach. We’ll never forget our time there and will look to rent again from owners that over the spectacular bonus. Thank you for granting us such beautiful memories.
Stayed 7 nights in Jul 2023
Archival

10/10 Excellent

A perfect place to stay, year after year ...

Time spent at The Tower House is like taking a step back in time where I feel transported to a more leisurely gracious pace of life. I instantly feel at ease in the spacious rambling Victorian house surrounded by a big expanse of lawn (ideal for croquet or just about any sport). I love the feel of the airy, cheery rooms (lovingly decorated with artwork and beautiful bedding). The light is spectacular in and out. The front porch is perfect for afternoon tea bathed in sunset light. The back deck is perfect for just about anything … outdoor meals, reading, napping, bird watching … but one of my favorite pastimes is simply soaking up the breathtaking unobstructed vista and expansive view of Menemsha Pond. The updated kitchen is cook and company friendly and a great place to gather a large group in the morning and end of day. I’ve slept in almost all of the bedrooms and each one is welcoming. If we can tear ourselves away from the house … the choice of private beaches is an especially cherished perk of the house. Lovey’s Beach is walking distance from the house, and a favorite place for an early morning or sunset walk. The access to Hancock Beach is one of the most anticipated repeat experiences. It rates as one of the top beaches I’ve ever visited – as good for walking along the water’s edge as swimming. A majestic setting that leaves an indelible imprint. It’s been fun to see the local food movement develop over recent years … and there are any number of small farms where you can pick up fresh vegetables, cheeses, and meats either directly at the farms or at the farmers markets. This is a place that I look forward to visiting again and again – both for the familiar pleasures as well as exploring and discovering new ones. It’s a little piece of heaven. And it seems to get better each time I visit.
Response from VrboOwner on 27 March 2020
We're delighted that you and your family enjoy so many of the welcoming elements that make the Tower House and its hilltop location a place where guests feel simultaneously special and at home!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Magical Wedding week

This was our second visit to Lovey's cottage, and our first stay at the Tower House. Robert is a great host and his property is outstanding. We were hosting our daughter and son-in-law's dream wedding. The views, the grounds, the location, the tasteful attention to detail, and the quality of accommodations are all first rate. The house is filled with light, art, and character. Space for large meals around a beautiful table, a porch for morning coffee and afternoon drinks. I was very pleased with the overall condition of this much loved and enjoyed property. All communications were smooth. I cannot imagine a better week, still basking in the glow. We have been renters on the island for 30 years, and this stay exceeded our expectations. Thank you Bob for sharing the Tower House with us all, we have created memories for a lifetime. And we hope to come back for a visit real soon.
Stayed 7 nights in Sep 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful family memory!

We had a wonderful time at this Martha’s Vineyard home. Many memories were made with our family and we will always cherish our time out there! Chilmark is such a hidden gem and the property has enough activities that you really don’t need to leave!
Stayed 7 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Visit

This was our second year coming to the Tower House with a big family (including grandparents and young children). What a wonderful place to spend a week. Beautiful views from the deck, spacious kitchen and living areas, clean and spacious bedrooms, and fantastic private beaches (as well as proximity to many great public beaches). And the Up Island location is a delight.
Stayed 7 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Welcome Retreat From The Busy World

Five large bedrooms plus a welcoming kitchen, dining room and den offered our family plenty of space to decompress and unwind. The steady ocean breezes through our windows were heavenly. We spent most of the time on the deck that faced the ocean. Every morning we congregated around the large kitchen table while the cooks among us fixed breakfast. We drove from home (Virginia) while some of our guests flew in directly. Renting a car for a week on the island is pricey so bringing your own car is a wise move. At least one car is a must as the nearest grocery store is 15 minutes away. Found the kitchen well stocked with lovely dishes and cooking utensils, but guests must supply their own food. That is a challenge on Sunday when many stores are closed. Chilmark is quiet. One must drive 20-25 minutes to the action in Edgartown and Oak Bluffs if that is what is desired. As guests in the Tower House we had access to lovely private beaches. The owner was very responsive and answered all our questions in a timely manner. He was especially helpful when explaining the process of how to get a ticket on the auto ferry which must be done months in advance. It was a beautiful home and we enjoyed it very much.
Stayed 7 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spectacular location

A lovely house, great views, a cooling breeze and a family -friendly layout; the house was everything we hoped for.
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay at Tower House

Our family had a wonderful time enjoying this great property. The house was comfortable, and the views from the back deck were amazing. A great up-island location. Thanks for a wonderful stay!
Stayed 7 nights in Aug 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great views; Well-thought-out house; Helpful host

We loved this house. We were a bit concerned a because we had never rented so far out on the island, but loved every moment of our stay. Being a long way from a supermarket was more than made up for by the peace and quiet and gorgeous scenery. The kitchen was very well appointed - the best of any house we have rented. The rooms are very tastefully decorated. We've rented places on the Vineyard before, and owners have decorated it with gewgaws and touristy trinkets and bought uncoordinated furniture, but not here! All in all, a fabulous stay!
Stayed 7 nights in Aug 2021
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Family retreat with incredible views.

We loved our stay and could not believe the setting…..it was magnificent! The house was large, well provisioned, and comfortable. The second floor bathroom leaked into the foyer so we severely limited our use of the shower. Additionally the window screens could use some caulking to reduce the number of bugs in the house. I would highly recommend Tower House for large family gatherings and will treasure the many memories we made during our two week stay. Bob, our caretaker, was extremely helpful and very timely in his response.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chilmark

The location is fantastic! Grand old Cape Cod building.
Stayed 7 nights in Aug 2020
Archival

10/10 Excellent

Take me away to my Happy Place

Exceptional Property. We’ve long been enjoying our time at this property as repeat summer guests. A much-loved family tradition! We take the big main house as well as the smaller guest house (Lovey’s Cottage), which allows our 3-generation family a lot of flexibility. Here’s what we enjoy about the Tower House, specifically: - The house is beautifully kept – well-furnished and maintained. And we love being part of its special history! - Such a spacious feel – and lots of light -- in all the rooms (comfortable beds in the bedrooms!) - The kitchen’s big and sunny, very inviting. And the huge back hang-out deck…sublime. - Fabulous view: all the way to Menemsha fishing village, and past the islands beyond. - The property’s big, private grounds. Great for kids running around, exploring, and just having fun. - Having Lovey’s Cottage guest house on the property, which we also really enjoy renting, for smaller family groups, and our guests. - The 2 private beaches are a big deal for us… Lovey’s beach (fantastic for small kids), and Hancock beach (wow, no crowds!). - 3 other public beaches only minutes from the house: Squibnocket, Lucy Vincent, and Aquinnah. - Wonderful restaurants within a 5-10 minute drive: Outermost, Chilmark Tavern, HomePort, Beach Plum. - A lot of nice island walking trails in close range of the house. - Grocery stores, gas, library, community center (with kids’ programs), farm stands and fish markets all in Chilmark and nearby Menemsha.. These are some of the best weeks of every summer for us.
Archival

10/10 Excellent

Dream Come True

What a gem! The solemn stateliness of this historic home's exterior is matched by tasteful and modern comforts inside-- wifi, well-equipped kitchen, bathrooms, bedrooms and tons of spacious, yet cozy common areas. The entire house is styled w/ great original paintings and an artist's eye for color and style. As for the hilltop grounds, and the NONSTOP VIEWS --simply as good as it gets. For us, Chilmark is the perfect location; we revel in its tranquility and natural beauty, and we can always hop in the car for a short drive when we're jones-ing for some (commercial) Vineyard action. Manager was helpful and attentive.
Archival

10/10 Excellent

perfect for a wedding

We rented the house the Wednesday before our wedding through the Wednesday after. Our wedding party used the house and the cottage next door leading up to our Saturday wedding and our parents and families used the houses after the big day to wind down. Everybody only had wonderful things to say about these beautiful beach cottages. We had our wedding reception in a tent on the lawn and our cocktail hour near the deck overlooking Mememsha pond. Not a lot of people who come to the Vineyard for a weekend get to see the beauty of up island and it was amazing to have our own little piece of this paradise for the week to show our guests. I look forward to hopefully renting again with our family someday!
Response from VrboOwner on 27 March 2020
Our warm Congratulations on your wedding! We're delighted you so enjoyed our property, its widespread lawns, extensive views and its ability to accommodate you, your parents and many of your close family members for the week -- as your party combined the use of the big main house and the on-site guest cottage also! Quick question though -- we weren't sure about the 'beach cottages' you mentioned, as our property with its two houses crowns a hill (though it overlooks several beaches -- and offers private access to 2 others!). Regardless, we're certainly appreciative that you chose to celebrate your wedding surrounded by the real beauty of up-island, and in "our own little piece of paradise" -- which you made your own, and were able to show and share with guests in your wonderful wedding week! We welcome you back with your family, in years to come!
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